Significant Days
by Slightly Sassy
Summary: A glance into the days that moved Oliver Queen and Felicity Smoak from enemies to friends to lovers... With a bit of help from Diggle and Tommy. Olicity Secret Santa for Holysmoakingqueens


**A/N: Merry Christmas (or Happy whatever holiday you celebrate) Tatiana! I figured, especially after the angst of the mid-season finale, you deserved a little bit of fluff. So,**

 **hope you enjoy this mess of Olicity fluff and here's to another year of bliss for Oliver and Felicity. Inspired by** **this** **(** **/post/135418898474/remember3x20-i-fell-in-love-with-my-best-friend)** **amazing gif set on tumblr courtesy of remember3x20. (Also I added Tommy because if I'm doing fluff, I'm going to go all the way.) And I really hope you like long fics because somehow this turned into a monster without my permission so there's that.**

 **Significant Days**

 _June 14, 2008_

"Do I have to Dig? I don't know what you see in the 2 of them."

"Yeah yeah I know, you think they're terrible Casanovas. But you're the one who wanted to borrow the car and the only way you're going to get the keys is if you come pick them up."

"Ugh fine! But you owe me!"

"Owe you?! You're the one who wanted to borrow my car – and you've already hung up haven't you?"

There was only silence on the other end. _Thanks Felicity._

"Let me guess, Lissy on the other end?" The blonde asked with a wry grin.

"How would you possibly guess that Ollie? Was the line about us being terrible Casanovas?" His friend chimed in.

John Diggle could only give both of them blank stares. Sometimes even he wondered why he put up with the two of them.

"You know, she wouldn't hate you so much if you didn't relentlessly – and obnoxiously I might add – flirt with her every chance you get."

"Not our fault that your step sister is super hot Dig!"

Oliver must have been immune to all the glares that Diggle sent his way daily. He only rolled his eye and grinned again.

"I feel the need to add that she doesn't necessarily hate me. She finds me charming on occasion. Ollie is the one she truly hates!"

"Shut up Tommy" Both Dig and Oliver said.

Neck deep in left over fries and empty drink cups Dig heard a voice to his right.

"This is a real cute look for you."

Dig paused to wipe the ketchup from his chin and dangled the key off of his index finger. "You wanted these didn't you?"

"Oh thank you for being the best step-brother that I could ever ask for, constantly making such sacrifices for his little sister like lending her his car for her to go pick up the pieces for the computer she offered to build for him."

Tommy and Oliver were suspiciously quiet during this exchange. "Hey Lis!" _There was the interruption._ "You want to come to my party tonight? Dress code is optional. If you know what I mean."

"It's Felicity, a third grader would know what you mean, and in your dreams!"

"You most definitely do come in my dreams." Oliver sometimes had the mental capacity of a 12 year old. He could charm the pants off of any girl but whenever it came to Dig's sister, he reverted back to basically pulling her pigtails to get her attention.

"Ugh! You're lucky I don't file for sexual harassment _Ollie_."

Once again Dig rolled his eyes. Any normal person would shrink away from Felicity's loud voice but just leaned into it.

"You know you love our banter Smoak." When she didn't reply and just walked away, Oliver yelled after her, "Good bye Lis!"

 _October 15, 2009_

"Do tell me again why you decided to take a first year programming class in your last year? It's not like you need the credit for your degree."

"Because I thought it'd be an easy grade!" Came a whine, muffled from landing face first in a pillow.

Felicity rolled her eyes, "Oh don't be such a drama queen! And honestly, I don't know what gave you the idea that programming is a breeze. I know I'm good but I didn't think I made it look that easy!"

"Wow so humble." Oliver finally sat up, glaring at the girl currently spinning around on his desk chair.

"When you're as good as me, you don't need to be humble."

"I'm going to remind you of that next time you bitch me out for bragging about my sex life."

"I have seen no empirical evidence about that fact." Felicity laughed.

"1) was that a smile to a comment on my sex life? How far we have come! And 2) you are more than welcome to get some first hand evidence."

"And of course we're back to you hitting on me. I really thought we had made progress. Back to work, Mr. Queen."

It was Oliver's turn to grin and he opened his computer once more to work again. Barely 5 minutes had passed before Oliver was lying back down on his bed.

"Would you concentrate on the assignment? Or is that frat party downstairs killing your brain cells?"

Truth be told, Oliver had not been paying attention to the thumping bass running through his dorm. But he was content to let Felicity believe that his lack of concentration was because of the prospect of the party downstairs not any of the pressure of his impending future. After all, it wouldn't be good for her to think he was an actual human being with emotions and shit.

"Okay all joking and banter aside, that's the 7th time in the past hour that I've seen you make that face. What's with it?"

"Nothing, just can't wait to get to that party once I finish this assignment."

Even a complete stranger could see through the grin that Oliver gave her. "That's bullshit and we both know it Oliver."

He started at the sound of his name; he didn't think she had actually called him by his name before, "Hey they do say it's easier to tell things to a stranger. And we're practically strangers. Feel like trying out the whole talking about your emotions thing?"

If it had been any other person, Oliver would have blown them off completely. But as it was, he knew Felicity was an incredibly trust worthy person – she had basically been raised by one of his best friends – so he thought _What the hell?_

"Honestly, its graduation. And everything that's supposed to come after it."

Felicity may pretend to hate the guy, but she knew there were some redeeming qualities in him otherwise John wouldn't hang out with him almost every day. Listening to him talk about how he felt the pressure to become a Robert Queen 2.0 and take over Queen Consolidated the second his graduation cap was off his head. He told her about how Tommy and him wanted to open a nightclub, take their love of partying into something productive and break the molds built for them by their fathers.

"Do it."

"And I just want to have something that's my own, you kn – wait what?"

"I said do it. Oliver you talk a lot of shit most of the time but this is the most honest thing I have ever heard you been. Do it and don't quit. Don't let what anyone says about you stop you. For once in your life work hard for something and it will be the greatest thing you've ever accomplished."

"Don't think I didn't notice you slip in that little insult there but, even with it, I think that's the sweetest thing anyone has said to me. Thank you Felicity." He smiled at her and she smiled back.

"Well don't get used to it, letting you know now that tomorrow I'll be back to mocking you for having to get programming help from a 17 year old, Ollie"

"I wouldn't have it any other way, Lis"

 _February 23, 2011_

Oliver was a sucker. That was a fact. For someone who was afraid of commitment, it was almost ironic that his longest lasting relationship with a girl was a friendship with his best friend's little sister. And he wasn't getting any sex out of the deal. And he was in love with her so there was that.

" – and he talked about his cockroach collection the whole night! I'm not going on another blind date set up by John ever again. It always ends badly."

"We became friends, didn't we?"

"Oliver you realize that you aggressively fake flirted with me constantly and I constantly considered stabbing you through the eyes with a ball point pen."

Sipping on his coffee, he burned the roof of his mouth. " Wait wait wait."

Her eyes widened, "What what what?"  
"I was never fake flirting! I mean I'll be the first one to admit that I was a terrible human about it. But if you had ever said yes, I would have totally jumped on that."

Felicity could not stop laughing, "Jumped on that? Wow I feel so flattered."

"No I didn't mean it like that!"

"Calm down Oliver!"

"No but actually, I really want you to understand. I liked riling you up but I was never stringing you along."

"Okay, I get it, you thought I was hot. Not that I blame you!"

Nothing Oliver could say would allow Felicity to realize that he was being serious. However, that was okay because he had her friendship. Dear god he was hopeless.

"Now back on topic, Oliver the date was terrible! And it's the third one this month. I swear Dig has to get higher standards for me."

Oliver covered the hand that was holding her coffee, "Should we really trust Dig's dating advice? He is wrapped around Lyla's finger with their strange on-again-off-again arrangement."

"Fair enough Oliver."

 _May 6, 2012_

"Maybe they've finally figured out the on-again-off-again deal!"

"I give them a year."

"Your faith in your brother's happiness is great."

Felicity smiled despite of herself, "Happy marriage is a myth."

"I look forward to proving you wrong."

"For that to happen you would have to actually get married Oliver." Oliver smiled but felt his heart pang. Although he tried to not to think too hard about why he felt that way.

There was a beat where only the music played and then, "They do look happy don't they?"

Oliver glanced over at the newlyweds. It was as though no one else was in the room they were so wrapped up in each other's eyes. "Yeah I think they are."

Another beat passed, "Dance with me." Felicity looked surprised at Oliver's outstretched hand.

"What."

"Come on, don't make all my mother's dance lessons go to waste, Felicity."

She smiled at him, grabbed his hand, and pulled him onto the dance floor.

Like every cliché in every romance movie ever, the song changed to a slow one as they moved. Oliver twirled her into his chest and moved her other hand to his shoulder. _When did his hands get so large,_ she asked, taking note of the fact that it spanned her entire back. It wasn't unusual for Oliver to place his hand on the small of her back when he walked with her somewhere, but it wasn't normally over a thin silky bridesmaid dress.

As the music played she rested her head on his shoulder. _Dear god it was well structured and muscled._

"Why thank you Felicity."

Felicity felt herself go stiff in his arms. "Did I say that out loud? Can you have temporary amnesia please?"

"Sorry to disappoint. But thank you for noticing," He said with a laugh. "Your brother's been killing me with our sparing lately."

"That's what you get for being best friends with a martial arts teacher. You get your ass kicked."

"Don't ruin the moment."

"Oh I'm sorry, were we having a moment? My bad." And as the night continued the only thought running through his head was as ridiculous as this girl was, he was so gone on her.

 _March 1, 2013_

It was their one rule: once a month there had to be drinks. Not everyone could make it every time but they all tried their best to stay in touch. This time Tommy was off with his girlfriend so it just happened to be Dig, Oliver and Felicity.

"Look at us." Dig started.

"Uh oh it's about to get sappy in here." Oliver snorted.

"It's just, I'm married, Felicity is dat- sorry, casually sating Ray and Oliver is in love with the perfect girl."

Felicity leveled Oliver with a flat stare, "He needs to tell her for that to count."

"I'm working on it."

"Come on share some more Oliver! I've heard basically nothing about her!"

The last thing in the world Oliver wanted to do was talk about how he was in love with Felicity to Felicity. It was painful enough hearing about her go on about the dates with Ray and how amazing he was.

"There's not much to tell… She's actually kind of in a relationship right now so I'm keeping my distance. Plus I don't deserve her even if she was single" Oliver said, avoiding eye contact with Diggle. However, despite his best efforts, their eyes still met across the table. Oliver immediately knew that Dig was well aware about who this so-called 'perfect girl' was.

"Now you listen to me nice and clear Mr. Queen," Both Dig and Oliver sat up a little straighter in their seats at the hint of the Loud Voice. "You may have been an absolute tool when you were younger – "

"Thanks Felicity."

" – but you have really grown into a mature man. Just look at you now, not trying to be jealous caveman but instead letting this girl make her own decisions in life. You care more about her happiness than your immediate happiness, which never would have happened a few years ago.'

'And say what you will, but if this girl is as amazing as you say, then you most definitely deserve her. Am I understood? Don't let your past define you as a person, okay Oliver? And if anyone has a problem with that then you tell them to come to me and I'll knock some sense in them."

Oliver's smile softened. Even at the worst times in his life, when no one believed in him, he could always count on Felicity to be on his side.

"Yeah Felicity, you're understood."

 _July 11, 2014_

Oliver wasn't always a morning person. There was a point in his life when he wouldn't have gotten out of bed before 11 for the apocalypse. Those days were now gone. After discovering the joys of morning workouts, Oliver found himself ready to go at 7 in the morning without fail. However, when he awoke this particular morning he knew he wasn't going to get up to go on his usual run.

Spread across the pillow beside him was a rat's nest of blonde hair. He admired the state of its' mess, the result of the number of times he ran his hands through it. After someone looks at something long enough, when they're finally allowed to touch they're going to go all out. As his eyes scanned down the naked body he smirked, _that attitude certainly explained the number of hickeys she had this morning_.

The warm body beside him stirred and he froze. _What if she thought it was a mistake?_ The thought had not crossed his mind the night before. They had been having one of their usual movie nights and Oliver had made some joke. It wasn't even that original but for some reason she reacted as though it was the funniest thing she had ever heard. Listening to her laugh so hard she snorted Oliver realized he had to tell her how he felt.

He had been listing reasons why he couldn't for years now. She hates you, she deserves better than you, she's with Ray right now, they just broke up, she isn't ready… But Felicity was a remarkable person and someone was going to realize it eventually. Oliver knew he wouldn't be able to watch her ride off into the sunset with someone else.

Her giggles dying down, Oliver had turned to her, "God I love you." _That wasn't what he meant to say_.

Immediately her giggles stopped. Felicity looked over into Oliver's eyes. She must have found what she was looking for because next thing he knew she was leaning over and kissing him on the lips. For almost a full minute he couldn't respond because he didn't feel like it was real. Just as she was about to pull away, his hand came up to cradle the back of her head and he pressed in further.

From there the rest of the night was a blur of clothes being removed, skin on skin, and soft brushes of lips. It could not have been more amazing.

"Ol'er?" Felicity's hand came up patting the bed until she found his chest. "Cuddle plus sleep." And who was he to deny her.

About 2 hours later Felicity stirred again and rolled over to face Oliver. The tension in the silence grew until Felicity broke it.

"So last night."

"Yeah." _Wow Oliver so eloquent way to impress the girl._

"Do you regret it?"

"No!" Oliver cried immediately. "Do you?"

Felicity toyed her lip with her teeth, "No. But what about your perfect girl?"

"Were you not listening? Felicity. You are my perfect girl."

The smile that she gave him could have lit up an entire city block. And just like that Oliver could feel his heart lift in his chest and skip a beat.

"Oh thank god!" Oliver's grin only got wider. "Because I've been in love with you for about 2 years now and I was about to cry if I had to give this all up again."

"I think I have you beat at about 5. But also, what do you mean 2 years? Just last year you were dating Ray if I remember correctly and, trust me, I do."

Felicity couldn't help but look bashful. "I didn't think it was ever going to be like that between the two of us. So I resigned myself to having to try and move on from you."

Oliver rolled on top of her and took in her beard burn and the collection of purple marks running down her neck. "We are the biggest of idiots." From there, there wasn't much talking.

 _December 21, 2015_

"I want to spend the rest of my life learning the mythology of a happy marriage with you."

"Are you sure? I've been told that I'm very aggressive in study groups."

"I sure hope so."


End file.
